Dimethyl methylphosphonate → Dimethyl (3-fluoro-2-oxoheptyl)phosphonate
Reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.[F:13][CH:14]([CH2:19][CH2:20][CH2:21][CH3:22])[C:15](OC)=[O:16]>C1COCC1>[F:13][CH:14]([CH2:19][CH2:20][CH2:21][CH3:22])[C:15](=[O:16])[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Dimethyl methylphosphonate (8.38 g) was dissolved in dry THF (250 ml) and cooled to -78° C. n-Butyllithium (1.6-M, 42 ml) was added dropwise, and the reaction was stirred for 10 minutes. The above methyl fluorocaproate (200 g) in THF (10 ml) was added dropwise. After addition, the mixture was stirred at -78° C. for 45 minutes, and then at room temperature for additional 45 minutes. The crude product obtained after the conventional work-up was chromatographed (hexane/ethyl acetate=1/1).